Facebook’s courtyard, with company motto.

Facebook, Twitter, and Paying for the Internet

An annotated index

If you’re committing career suicide, best to leave an extensive note.

This week my tell-all memoir Chaos Monkeys is published by HarperCollins. Having founded a company acquired by Twitter, which I immediately abandoned for an early role on Facebook’s Ads team, only to once again return to Twitter after a tumultuous time at FB, I’ve decided to set down on paper (real, not metaphorical) my time inside the Silicon Valley washing machine. Since I’m violating both written and unwritten codes of silence around divulging the often dark inner workings of these tech behemoths, as well as Valley hangers-on like investors, I have every expectation of being completely unemployable for the foreseeable future. If you jump into the abyss, you jump headlong.

Here’s a sample of the book’s index, complete with marginal (in both senses of the word) commentary. Click on the asterisk to the right and mouse over the note to highlight the entry in question; then, scroll to the bottom of the piece and click “see all responses” for the full set. Bolded entries are the ones with annotations.

To those mentioned who feel I misconstrued events, either in this index or Chaos Monkeys itself: I invite you to write your own competing account. Together we may arrive at the set of mutually agreed-upon lies called history.

Note: Some names have been omitted to protect the truly guilty.

Badros, Greg, 3, 410, 454, 457
Bain, Adam, 184, 188–90, 203, 478–79, 494
Baker Scholar, 110
Bakshy, Eytan, 368
bar-code reading, 51
batch, 105
Battles, Matt, 430
Beacon, 335
bedroom communities, 338
beer and diapers, 363
Beltway Boomers, 385
Belushi, John, 399
Best Buy, 328
best effort, 418
beta products, 44
Bezos, Jeff, 428
Big Brother, 384, 402
Bin Laden, Osama, 384
birth, 59–60
black-hat hackers, 314 
Blackwell, Trevor, 60
Boland, Brian, 382, 398
 first meeting, 3–4
 in great debate, 459–61
 on integration, 443
 middle manager, 463–64
 reporting to, 277
 seducing, 408
 slides, 7–8
 stripping of duties, 452
Bolshevism, 356
boot camp, 269
Bosworth, Andrew (“Boz”), 2, 444–46, 457–60, 473–74
Boyd, John, 436, 437
The Boy Kings (Losse), 445
brand advertising, 39–40
Brazil, 377–78
Brazil, Alan, 22–23
British Trader
 babies, 58–59, 170, 304–5
 child support to, 306–7
 family, 84
 meeting, 54–56
 relationship, 165, 168, 245
Brogramming, 400
Graham, Paul (“PG”)
 advice, 231
 essay, 46–47, 52–53
 first meeting, 90
 genius guru, 98
 meeting with, 60–62
 mythologies, 99
harassment, 66–68
Hart, Camille, 4–5 
hashing, 387
hate speech, 315
Hemingway, Ernest, 106
Herodotus, 421
Herzl, Theodor, 496
Hoffman, Reid, 88
hogrammers, 400
home-brewing, 406
Palihapitiya, Chamath, 265–66
Palo Alto
 bosom of,
 116 climate, 123
 downtown, 333, 338
 East, 404
personally identifiable information (PII), 395
PMMess, 347–51, 407, 409
poker playing, 396–97
polyandry, 483
Polybius, 172, 316, 336
Pong, 150
Ponzi scheme, 16
pornography, 167, 262, 268, 312, 314, 315

pregnancy, 58–59
product managers (PMs)
 as Afghan warlords, 273
 earning money, 302
 everyday work, 294
 Facebook, 4, 6–7, 10, 91, 97, 202, 210, 271–79
 Google, 192
 habitat, 341
 high-value, 246
 ideal, 219
 information and, 295
 internal and external forces and, 316–17
 last on buck-passing chain, 327
 managing, 276
 stupidity, 313
 tech companies, 272
 tiebreaker role, 292
Rabkin, Mark, 3, 312, 389, 398, 435 
Rajaram, Gokul, 8, 10

 accepting offer from, 248
 banter with, 472–73
 as boss, 3
 bribery, 471
 go big or go home ethos, 300
 in great debate, 459
 influence, 202
 insubordination toward, 465
 interview with, 221–22
 leadership, 309
 loss of trust, 468
 lot with, 373
 management of, 434
 middle manager, 463–64
 one-on-one and, 469
 as product leader, 276–77
 stripping of duties, 452
Ralston, Geoff, 93
Rapportive, 96–97, 106
real-time bidding (RTB), 40–41 
real-time data synchronization, 38
Red Rock Coffee, 84
RedLaser, 51
Reesman, Ben, 308, 389, 399–400, 475, 477
relativity, 25
replicating portfolio, 247–48
retargeting, 9, 381, 395, 438, 461
return of advertising spend (ROAS), 81 
revenue dashboards, 274–75, 295–96 
The Road Warrior, 134
Roetter, Alex, 185, 190, 493–94 
romantic liaisons, 55–56
Romper Stomper, 202
Rosenblum, Rich, 21–22
Rosenn, Itamar, 368
Rosenthal, Brian, 389, 390
Ross, Blake, 444
Rossetti, Dante Gabriel, 303
rounds, 156
routing system, 324
Rubinstein, Dan, 312–13
Ruby on Rails, 155
Russia, 375–76
Sacca, Chris, 128, 141, 143
 acquisition advice, 187–88, 212–13, 245–47
 on deals, 205–7
 ignoring inquiries, 201

 pseudoangel, 113, 117–19
 wisdom, 202
safe sex, 58
sailboat living, 307, 332, 337–38
Sandberg, Sheryl, 2, 10
 data joining and, 465
 gatekeeper, 4–5
 intimates, 3–4
 leadership, 410
 managerial prowess, 311–13
 meetings, 371, 382, 459
 PowerPoint and, 7
 recommendations to, 462
 schmoozing, 367
 wiles of, 408
sausage grinder, 296
Scalps@Facebook, 314
scavenging foray, 116
schadenfreude, 16–17
Schopenhauer, Arthur, 282
Schrage, Elliot, 3–4, 410
Schreier, Bryan, 123–25
Schrock, Nick, 400

Schroepfer, Mike, 2
Schultz, Alex, 374
scientific racism, 122
Scoble, Robert, 100
Scott, George C., 24, 369
security, 314–15
seed money, 96
Sequoia, 122–25, 130, 159
severance package, 470–71
severity-level-one bug (SEV1), 323
sexual molestation, 17
Simo, Fidji, 348, 483
single-trigger acceleration, 254 
skulduggery, 69, 229 
social mediation, 496
social mission, 257
social plugins, 6–9
The Social Network, 282, 288, 333
software
 ad-blocking, 325
 Adchemy, 43
 analytics, 448
 building, 47, 155
 bundling, 149–50
 chaos monkey, 103
 conversion-tracking, 222
 development, 455
 enterprise, 153
speed eating, 21
Sponsored Stories, 280, 365, 367, 369–70, 444
Spotify, 362, 364–65 
SQL write command, 323 
Square, 464
stack, 439
Stanford, Leland, 121
Tai, Bill, 126–28
Taleb, Nassim Nicholas, 197 
targeting

 ability, 393
 accountability and, 39
 ads, 4, 7, 274, 280, 299, 320, 323, 398, 402, 412, 440, 479
 clusters, 395
 data, 318, 485
 defined, 274
 Facebook, 321, 362, 368, 438, 442
 functionality, 327
 hashtags, 293, 295
 magic, 10
 political, 302
 quirks, 477
 retargeting, 9, 381, 395, 438, 461
 running, 459–60
 segments, 292, 295, 322, 385, 423, 452
 teams, 276, 296, 301, 346, 390, 401, 452
 topics, 296
tech boom, 121, 181, 336, 495 
tech bubble, 155, 181, 224, 247

tech companies
TechCrunch, 43, 175, 255 
technical debt, 455 
Technofuturism, 356 
technolibertarians, 491 
technology. See also software
 development, 294
 Internet advertising, 429, 446, 454
 Silicon Valley, 294
TellApart, 426
Tesla, 241–43, 339
texting, 161, 490–91
Thau, Kevin, 202, 245, 249 
third-party data, 390, 423, 440, 484 
This Old House, 56
Thompson, Hunter S., 241
Tillman, Matt, 241–43
Timberlake, Justin, 333
Time magazine, 287
Tinder, 103
track racing, 344–45
Trada, 83
Tretola, Dan, 349
TriplePoint Capital, 129, 143–44 
truth, 457–58
Turn, 390
Twain, Mark, 66
Wall Street
 bonuses, 27
 pursuit of gain, 23–24
 Silicon Valley paralleling, 27
 traders, 89
Wall Street Journal, 261, 325, 354
Walmart, 49, 96, 349, 385
Wang, Ted, 138–39, 145–46, 152, 192 
Warhol, Andy, 261
Washington Post, 364
Webster, Daniel, 14

Weil, Kevin, 190, 478–79, 481
 first meeting, 185–88
 reporting to, 234
 second meeting, 238
 in Twitter shake-up, 493–94
Weinstein, Scott, 29–31 
WhatsApp, 490–91 
Whereoscope, 202 
Wiesel, Elie, 16
Wiesel, Elisha, 16
Wi-Fi, 339

Williams, Ev, 177, 183, 196
Wilson Sonsini Goodrich & Rosati, 134 
Windows, 47, 286
Winklevoss twins, 151
Zeitgeist, 29–30
zero-sum game, 230, 319
Zoufonoun, Amin, 209–11, 213, 225–26

Zuckerberg, Mark (“Zuck”)
 advertising knowledge, 393–94
 on clown car, 428–29
 company-wide Q&A, 348–49
 on connected world, 285
 court of, 444
 declaring Lockdown, 287–89
 e-mail from, 353
 throne, 371

Excerpted from Chaos Monkeys: Obscene Fortune and Random Failure in Silicon Valley, published by HarperCollins on June 28, 2016. Available for purchase at Amazon, Barnes and Noble, or your local independent bookseller.